3-Chloro-2-hydroxypropyl dimethyl dehydroabietyl ammonium chloride: Synthesis, characterization, and physicochemical properties

Article abstract of DOI:10.1007/s11743-013-1490-0

3-Chloro-2-hydroxypropyl dimethyl dehydroabietyl ammonium chloride (CHPDMDHA) was synthesized from dehydroabietylamine (DHA) and epichlorodrin. The synthesis was done in three steps. First, DHA was transformed into N,N-dimethyl dehydroabietyl amine (DMDHA) through Eschweiler-Clarke Reaction. Second, the DMDHA was reacted with hydrochloric acid and translated into DMDHA hydrochloride. Third, the CHPDMDHA was obtained after the DMDHA hydrochloride had reacted with epichlorodrin and recrystallized using a solvent composed of ethyl acetate and ethanol. The critical micelle concentrations (CMC) of CHPDMDHA at 25 °C was found to be 2.56 × 10^-4 mol L^-1, and its surface tension at the CMC (γ_CMC) was determined to be 27.4 mN m^-1; these data suggest that the surface activities of CHPDMDHA are better than those of benzalkonium chloride (BC), so that CHPDMDHA could be used as a good alternative to BC.

Full text of DOI:10.1007/s11743-013-1490-0

J Surfact Deterg
DOI 10.1007/s11743-013-1490-0
ORIGINAL ARTICLE
3-Chloro-2-hydroxypropyl Dimethyl Dehydroabietyl Ammonium
Chloride: Synthesis, Characterization, and Physicochemical
Properties
•
Li-jun Pei Zhao-sheng Cai Zhan-qian Song
•
•
•
Xue-mei Zhu Shi-bin Shang
Received: 13 January 2013 / Accepted: 22 April 2013
Ó AOCS 2013
Abstract 3-Chloro-2-hydroxypropyl dimethyl dehydroa-
bietyl ammonium chloride (CHPDMDHA) was synthesized
from dehydroabietylamine (DHA) and epichlorodrin. The
synthesis was done in three steps. First, DHA was trans-
formed into N,N-dimethyl dehydroabietyl amine (DMDHA)
through Eschweiler-Clarke Reaction. Second, the DMDHA
was reacted with hydrochloric acid and translated into
DMDHA hydrochloride. Third, the CHPDMDHA was
obtained after the DMDHA hydrochloride had reacted with
epichlorodrin and recrystallized using a solvent composed of
ethyl acetate and ethanol. The critical micelle concentrations
(CMC) of CHPDMDHA at 25 °C was found to be
2.56 9 10-4 mol L-1, and its surface tension at the CMC
(cCMC) was determined to be 27.4 mN m-1; these data sug-
gest that thesurface activities of CHPDMDHA are better than
those of benzalkonium chloride (BC), so that CHPDMDHA
could be used as a good alternative to BC.
Introduction
Rosin is a natural chemical obtained from pine trees, and
its total output is multimillions of tons annually [1–6].
Rosin is mainly a mixture of C20 monocarboxylic diter-
penic resin acids including abietic-type acids and pymaric-
type acid. The percentage of these resin acids in the rosin is
ca. 90 % [1–3]. It also has a certain quantity of fatty acids
and other neutral components, and their percentage in the
rosin is ca. 10 % [1–3]. The rosin could be transformed
into disproportionated rosin, in which the percentage of
dehydroabietic acid is commonly higher than 50 %,
through disproportionation at 200 to 240 °C [2, 5–8].
Dehydroabietylamine (DHA) is a compound derived
from dehydroabietic acid [6, 9]. As a compound friendly to
the environment, many applications for DHA have been
developed, such as the synthesis of pesticides and phar-
maceuticals, the preparation of surfactants and corrosion
inhibitor, the manufacture of epoxy resins, and so on [9–
16]. Among all of these applications, the preparation of
surfactants using DHA as the basic material may be the
most important one.
Keywords Critical micelle concentrations ꢀ Surface
activity ꢀ Eschweiler-Clarke reaction ꢀ 3-Chloro-2-
hydroxypropyl dimethyl dehydroabietyl ammonium
chloride (CHPDMDHA)
DHA could be utilized to produce cationic, nonionic,
anionic and amphoteric surfactants, but the synthesis of
cationic surfactants, especially the quaternary salts, using
DHA as the starting material has been studied more
extensively [6, 15, 17, 18]. According to the literature [17–
19], it is known that the preparation of cationic surfactants
based on DHA could be carried out through a quaternizing
reaction, which could be as follows: (1) the DHA is quat-
ernized directly with a halohydrocarbon as the modifying
agent (2) the DHA is modified with an active quaternary
salt as quaternizing agent, and (3) the N,N-dimethyl
dehydroabietylamine (DMDHA), which is the product of
DHA after Eschweiler-Clarke reaction, is quaternized
L. Pei ꢀ Z. Cai (&) ꢀ X. Zhu
School of Chemical and Biological Engineering, Yancheng
Institute of Technology, Yancheng 224051, Jiangsu Province,
People’s Republic of China
e-mail: jsyc_czs@163.com
L. Pei ꢀ Z. Song ꢀ S. Shang
Institute of Chemical Industry of Forest Products, Chinese
Academy of Forestry, Key and Open Laboratory on Forest
Chemical Engineering, SFA, Nanjing 210042, Jiangsu Province,
People’s Republic of China
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CMC and cCMC Measurements
After dissolving a certain amount of quaternary salts in
demineralised water, half the solution was taken out from
volumetric flask and diluted with demineralised water by
the duplicate diluting method or the decuple diluting
method, and a series of solutions containing the quaternary
salt was obtained. The surface tension (c) of solutions with
different concentrations was measured with an JYM-200D
automatic tensiometer (Shipeng Testing Equipmen Co.,
Ltd of Chengde, PR China) connected to a thermostatted
water bath maintained at 25 °C, and three replicates were
performed in each case. The curves reflected the relation-
ship between c and the concentration (c) of the quaternary
salt as plotted, and the CMC and cCMC of quaternary salt
were obtained from the experimental curve.
Scheme 1 Route for the synthesis of CHPDMDHA
using halohydrocarbon. 3-Chloro-2-hydroxypropyl dime-
thyl dehydroabietyl ammonium chloride (CHPDMDHA) is
a cationic surfactant based on DHA, its structure is similar
to that of benzalkonium chloride (BC). CHPDMDHA may
be utilized as an alternative to BC and be applied for the
preparation of emulsified bitumen, emulsified silicone oil,
rosin emulsion, etc. Furthermore, because of the presence
of 3-chloro-2-hydroxypropyl in CHPDMDHA, it is possi-
ble to utilize CHPDMDHA as an active intermediate for
the synthesis of polymeric cationic surfactants containing a
dehydroabietyl group. However, to our knowledge, there is
no report on the preparation of CHPDMDHA. Herein, we
report the preparation of CHPDMDHA using method (3).
The physicochemical properties including critical micelle
concentrations (CMC) and the surface tension at the CMC
(cCMC) for CHPDMDHA were also investigated. The
preparation of CHPDMDHA is presented in Scheme 1.
Purification of DHA
After DHA (30.0 g) had been dissolved in 300 mL ethanol,
100 mL ethanol solution containing p-toluenesulfonic acid
(23 g) was added. The mixture was stirred at room tem-
perature until the reaction was completed, and then the
reaction mixture was allowed to remain for ca. 5.0 h
without stirring. The mixture was filtered and the solid
residue was recrystallized using ethanol. The dehydroa-
bietyl ammonium p-toluenesulfonate was obtained after the
crystalline solid had been dried under vacuum at 30 °C for
ca. 10.0 h, and its melting point was 256–258 °C.
The dehydroabietyl ammonium p-toluenesulfonate was
dissolved in 180 mL of distilled water under stirring before
200 mL toluene and 20 mL 15 % NaOH aqueous solution
were added. The toluene layer was separated from the
reactant after the mixture had been stirred vigorously for
1.0 h, and washed with distilled water several times until it
had become weakly basic. The toluene solution was dried
with anhydrous magnesium sulfate and concentrated using
a rotary evaporator under vacuum. The concentrated liquid
was dissolved by ether under reflux conditions and crys-
tallized at room temperature. The purified DHA was
obtained after the crystals had been dried under a vacuum
at 30 °C for ca. 10.0 h, and its mass content was 98.3 %
determined by HPLC and its melting point was 54–55 °C.
Experimental
Materials and Apparatus
DHA was purchased from the Wanjing New-material Co.,
Ltd of Hangzhou (Hangzhou, PR China); its mass content is
87.3 wt% determined by HPLC. Epichlorodrin, formic acid
and formaldehyde were purchased from Sinopharm
Chemical Reagent Co., Ltd (Shanghai, PR China). All other
chemicals were of reagent grade and used as received.
Fourier transform infrared (FT-IR) spectra were recor-
ded with KBr pellets on a Nicolet Nexux FT-IR 670
spectrometer. Sixteen scans at a resolution of 4 cm-1 were
Synthesis of CHPDMDHA
1
averaged and referenced against air. A H-NMR spectrum
was obtained with a Bruker AV-500 spectrometer at
500.13 MHz and measured in CDCl3 solution at
30 0.5 °C. A 13C-NMR spectrum was obtained with a
Bruker AV-300 spectrometer at 75.47 MHz and measured
in DMSO-d6 solution at 30 0.5 °C. All the samples were
dissolved in a 5-mm diameter tube at a concentration of ca.
20 mg/mL.
First, 22.84 g purified DHA (ca. 80 mmol) was dissolved
in 100 mL ethanol, then 27.6 g 80 % formic acid aqueous
solution (ca. 480 mmol) and 33.34 g 36 % formaldehyde
aqueous solution (ca. 480 mmol) were added dropwise in
sequence into the mixture with stirring, and allowed to
react at room temperature for ca. 1.0 h. The temperature of
the mixture was raised to 87 °C in order to ensure
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refluxing. The blending was allowed to react at this tem-
perature under stirring until the DHA had been exhausted
according to monitoring the result of thin-layer chroma-
tography (TLC) analysis, and the duration for this process
was ca. 12.0 h. The ethanol and water were removed from
the reactant using a rotary evaporator under vacuum, and
the remainder was mixed with 100 mL saturated NaCl
solution under continuous stirring. After the mixture had
been treated sufficiently using 153.6 g 15 % NaOH solu-
tion, it was transferred into a separatory funnel and
extracted with 70 mL toluene three times. The toluene
layer was combined and washed with 30 mL distilled water
three times before the toluene was reclaimed by distillation
using a rotary evaporator under a vacuum. The residual
substance was distilled under a high vacuum and distilla-
tion cut of 220–230 °C/0.67–1.33 kPa, DMDHA, was
obtained with a yield of 72.6 wt%. The mass content of
DMDHA was 85.7 wt% determined by HPLC.
concentration of Cl- in sample solution (m1) was ascer-
tained according to the standard curve. The content of
CHPDMDHA in product was calculated as follows.
Mass content of CHPDMDHA %
ðm1 ꢁ m0Þ ꢂ V ꢂ 442:51
¼
ꢂ 100
ð1Þ
w ꢂ 35:5
m1 mass concentration of Cl- in sample solution, g/mL. m0
mass concentration of Cl- in distilled water, g/mL. V vol-
ume of solution, mL. 442.51 molar mass of CHPDMDHA,
g/mol. w weight of sample, g. 35.5 molar mass of Cl-,
g/mol.
Results and Discussion
Structure Characterization
Then, 13.10 g DMDHA (ca. 40 mmol) was dissolved in
100 mL ethanol and mixed with 50 mL 10 % hydrochloric
acid. The mixture was reacted at 70 °C for 1.0 h before it
was concentrated using a rotary evaporator under a vac-
uum. The remainder was dispersed into 100 mL ethanol
before 20 mL epichlorodrin was added dropwise at room
temperature. The temperature of the reactant was raised to
90 °C and reacted at this temperature until the DMDHA
was exhausted determined by monitoring the result of TLC
analysis (the duration was ca. 48 h). After the reaction was
completed, the ethanol and remained epichlorodrin were
removed from the reactant using a rotary evaporator under
a vacuum. The residue was treated with 100 mL ethyl
acetate under refluxing condition and refrigerated at 4 °C
for 24 h. The mixture was separated by filtration and the
solid was recrystallized using a solvent composed of ethyl
acetate and ethanol (Vethyl acetate:Vethanol = 2.0:1.0). The
CHPDMDHA was obtained with an 82.6 wt% yield after
the white crystal was separated from the solution and dried
under a vacuum at 50 °C for ca. 12.0 h, and its melting
point was 193–196 °C.
The FT-IR spectra of purified DHA, DMDHA and
1
CHPDMDHA are presented in Fig. 1. The H-NMR and
13C-NMR spectra of CHPDMDHA are presented in Figs. 2
and 3, respectively.
In the FT-IR spectrum of purified DHA, the absorp-
tion bands at 3,393 and 3,328 cm-1 were assigned to
mN–H of primary amine, 2,927 and 2,865 cm-1 were
ascribed to mC–H of CH2 and CH3, 1,613 cm-1 was
assigned to dN–H of NH2, 1,600 and 1,498 cm-1 were
assigned to mC=C of aryl ring, 1,460 and 1,380 cm-1
were assigned to dC–H of CH3, 1,064 cm-1 was assigned
to mC–N of amine, 883 and 822 cm-1 were ascribed to
the dC–H of aryl, respectively. Compared with DHA, the
absorption bands reflected the mN–H and dN–H of primary
amine had disappeared in the FT-IR spectrum of
DMDHA, and the intensity of absorption peaks reflected
the mC–H and dC–H of CH3 had increased. A strong peak
at 3,424 cm-1 in the FT-IR spectrum of CHPDMDHA
was ascribed to the mO–H, 1,637 cm-1 was ascribed to das
of quaternary group, 2,956 and 2,855 cm-1 were ascri-
bed to the mC–H of CH2 and CH3, 1,465 and 1,371 cm-1
were assigned to dC–H of CH3, 883 and 821 cm-1 were
ascribed to the dC–H of aryl, 970 and 628 cm-1 were
ascribed to the dC–Cl respectively.
Determination of Product Content
1
The mass content of CHPDMDHA in the product was
determinated by Ion Chromatography (IC). A standard
curve reflected the relationship between Cl- mass con-
centration (m) and absorbing peak area (A) was obtained
through determining the absorbing peak area of a series
standard NaCl solutions whose mass concentrations had
been ascertained previously. The product of quaternary salt
(ca 0.2 g) was dissolved in a definite amount of distilled
water, then the solution was analyzed using IC and the
absorption peak area was obtained. Meanwhile, the dis-
tilled water was utilized as the blank analysis. The mass
The signal at 7.14, 6.99 and 6.86 ppm in the H-NMR
spectrum of CHPDMDHA were assigned to the hydrogen
of aryl ring, 0.87–1.90 ppm were ascribed to the hydrogen
of CH3 or CH2 that unconnected with aryl ring or the N of
the quaternary group, 2.35 ppm was ascribed to the H of
OH, 2.77–3.0, 3.20 and 3.71 ppm were ascribed to CH3,
CH2 or CH that connected with aryl ring, the N of qua-
ternary group or hydroxy.
In the 13C-NMR spectrum of CHPDMDHA, the signal
at 147.2, 145.5, 134.4, 126.8, 124.4 and 124.2 ppm were
assigned to the carbon of the aryl ring, 70.42 ppm was
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Fig. 1 FT–IR spectra of DHA,
DMDHA and CHPDMDHA
All these data indicate that the product resulted from
the reaction between DMDHA and epichlorodrin in the
presence of hydrochloric acid was 3-chloro- 2-hydroxy-
propyl dimethyl dehydroabietyl ammonium chloride
(CHPDMDHA).
Yield of CHPDMDHA
The correlation data between the Cl- mass concentration
(m) and the peak area based on NaCl are listed in Table 1,
and the standard curve is shown in Fig. 4. The IC spectrum
of CHPDMDHA is shown in Fig. 5.
From Fig. 5, we could see that the peak height was
189.9 ls and the half peak width was 0.250 min, the peak
area was 47.475 ls min. The mass concentration of Cl- in
the sample solution (m1) was 417.57 ppm according to the
relationship between the peak area and Cl- mass concen-
tration (m) shown in Fig. 4. Combined with the sample
weight and the volume of the solution, the content of
CHPDMDHA in the product could be calculated according
to Eq. 1 and this value was 98.32 wt%.
Fig. 2 1H-NMR spectrum of CHPDMDHA
ascribed to the carbon of methylene connected with the
ring and quaternary group, 47.9 and 47.2 ppm were ascri-
bed to the carbon of methyl connected with the quaternary
group and methylene connected with Cl, 18.1, 18.4, 29.7,
37.5 and 37.7 ppm were assigned to the carbon of meth-
ylene of cycloalkyl, 33.3, 35.0 and 39.5 ppm were assigned
to the carbon of the CH of the isopropyl and the tert- and
quaternary carbon of the dehydroabietyl group, 19.0, 24.4
and 25.7 ppm were ascribed to the methyl carbon of de-
hydroabietyl group.
Evaluation of the Surface Activity of CHPDMDHA
The surface tension values of aqueous solutions of
CHPDMDHA at different concentrations are listed in
Table 2, and the plot reflects the relationship between the
surface tension (c, mN m-1) and the concentration (C,
mol L-1) of CHPDMDHA is shown in Fig. 6.
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Fig. 3 13C-NMR spectrum of
CHPDMDHA
Table 1 The correlation data between Cl- mass concentration
(m) and peak area based on NaCl
m, ppm
586.1 472.3 358.2 241.9 184.5 83.1 12.9
67.43 54.09 40.67 27.03 18.41 8.92 1.43
Peak area
(ls min)
Fig. 5 IC spectrum of CHPDMDHA
Fig. 4 Standard curve of peak area and Cl- mass concentration
(m) based on NaCl
dimethyl benzyl ammonium chlorides (BC14) and hexa-
decyl dimethyl benzyl ammonium chlorides (BC16)
´
reported by Farıas and Gracia et al. [20–22], we could see
The critical micelle concentration (CMC) of CHPDM-
DHA in aqueous solution is about 2.56 9 10-4 mol L-1 at
25 °C and its surface tension at CMC (cCMC) is ca. 27.4
mN m-1. According to the data concerned with the CMC
and cCMC of benzalkonium chloride including dodecyl
dimethyl benzyl ammonium chlorides (BC12), tetradecyl
that the surface activity of CHPDMDHA in aqueous
solution is the best one among BC12, BC14, BC16 and
CHPDMDHA. Therefore, CHPDMDHA could be utilized
as a good alternative to benzalkonium chloride (BC) and
applications obtained for the preparation of emulsified
bitumen, emulsified silicone oil, rosin emulsion, and etc.
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surfactant, could be used many more applications than
those of benzalkonium chloride to some extent.
Table 2 Surface tensions of CHPDMDHA aqueous solutions at
different concentrations
C/mol L-1
lg C
c/mN m-1
Acknowledgments We gratefully acknowledged the support of the
National Natural Science Foundation of P.R. China (No. 31170543)
and the Research Fund of the Key Laboratory for Advanced Tech-
nology in Environmental Protection of Jiangsu Province (AE
201114). We also gratefully acknowledged the support of the China
Pharmaceutical University in analysis.
6.3 9 10-7
9.9 9 10-7
15.9 9 10-7
24.0 9 10-7
39.0 9 10-7
6.3 9 10-6
9.9 9 10-6
15.9 9 10-6
24.0 9 10-6
39.0 9 10-6
6.3 9 10-5
9.9 9 10-5
15.9 9 10-5
2.0 9 10-4
2.52 9 10-4
3.0 9 10-4
-6.20066
-6.00436
-5.7986
-5.61979
-5.40894
-5.20066
-5.00436
-4.7986
-4.61979
-4.40894
-4.20066
-4.00436
-3.7986
-3.6968
-3.5986
-3.52288
71.2
56.2
48.4
39.1
37.2
33.4
33.1
31.3
30.8
30.35
30
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Conclusion
3-Chloro-2-hydroxypropyl dimethyl dehydroabietyl ammo-
nium chloride (CHPDMDHA) was prepared by the reaction
between DMDHA and epichlorodrin in the presence of
hydrochloric acid. The analytical result of IC indicates that
the content of CHPDMDHA in the product is more than
98 wt%. The critical micelle concentration (CMC) of
CHPDMDHA and its cCMC in aqueous solution were
about 2.56 9 10-4 mol L-1 and 27.4 mN m-1 at 25 °C,
respectively. These data are lower than those of BC12,
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Zhao-sheng Cai is currently a professor at the Yancheng Institute of
Technology, PR China. He graduated from the Institute of Chemical
Industry of Forest Products in 2009 and received a Ph.D. degree. His
main study area is the synthesis and analysis of fine chemicals, the
development and utilization of biomass resource and surfactant,
chemical modification of natural materials.
Zhan-qian Song is an expert in forest chemical engineering, a
member of the Chinese Academy of Engineering, and chief scientist
at the Chinese Academy of Forestry. He graduated from the
University of Science and Technology of China in 1964. He is
engaged in research in chemical processing and engineering devel-
opment of forests. He has studied the chemical deep-processing and
engineering development of gun oleoresin in China.
Xue-mei Zhu is currently an associate professor at the Yancheng
Institute of Technology. Her main study area is the utilization of
biomass resource and interface chemistry.
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Shi-bin Shang is a professor at the Institute of Chemical Industry of
Forest Products, Chinese Academy of Forestry. He graduated from
the Institute of Chemical Industry of Forest Products in 1995 and
received a Ph.D. degree. He works in the Institute of Chemical
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and development of biomass-based functional polymer materials and
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Author Biographies
Li-jun Pei is doctorate was awarded by the Institute of Chemical
Industry of Forest Products, Chinese Academy of Forestry. His main
123